Novel palladium complex-catalyzed reaction of magnesium amides with allylic electrophiles
In order to develop an efficient method for the synthesis of higher order unsaturated tertiary amines, and also to explore a new method for the formation of C-N bonds, they have investigated the transition metal complex-catalyzed reaction of magnesium amides with electrophiles; the electrophiles selected for study included allyl ethers and esters, as well as sulfones, sulfides and quaternized allylamines. The effects of the nature and structure of the catalyst components, as well as of the reaction conditions, on product yield were examined in the case of the reaction of diethyl (bromomagnesium)amine with diallyl ether, and revealed that the highest yield of diethylallyl-amine (I) was achieved using Pd(acac)/sub 2/ (3-5 mole %) and Ph/sub 3/P (1:2) as catalyst in THF solution at 50/sup 0/C for 5 h. Other transition metal (Ni, Fe, Zr, Ti, Cu) compounds were also examined as catalysts, but the yield of (I) did not exceed 15% with these compounds. Bimetallic catalysts based on Zr (Cp/sub 2/ZrCl, Py/sub 2/ZrCl/sub 6/, (RO)/sub 4/Zr) and Ni (Ni(acac)/sub 2/ and NiCl/sub 2/) were successful in forming (I) from diethyl (bromomagnesium)amine and diallyl ether in 60% yield.
- Research Organization:
- Institute of Chemistry, Ufa, USSR
- OSTI ID:
- 5846317
- Journal Information:
- Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Vol. 36:2; Other Information: Translated from Izestiya Akademii Nauk SSSR, Seriya Khimicheskaya; 36: No. 2, 406-409(Feb 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMIDES
CATALYSIS
CATALYSTS
COMPARATIVE EVALUATIONS
MAGNESIUM COMPLEXES
PALLADIUM COMPLEXES
CATALYTIC EFFECTS
ACETIC ACID ESTERS
CHEMICAL REACTION YIELD
COPPER COMPLEXES
GRIGNARD REAGENTS
IRON COMPLEXES
MAGNESIUM BROMIDES
NICKEL COMPLEXES
NMR SPECTRA
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
TETRAHYDROFURAN
TITANIUM COMPLEXES
ZIRCONIUM COMPLEXES
ALKALINE EARTH METAL COMPLEXES
ALKALINE EARTH METAL COMPOUNDS
BROMIDES
BROMINE COMPOUNDS
CARBOXYLIC ACID ESTERS
COMPLEXES
ESTERS
FURANS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
MAGNESIUM COMPOUNDS
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SPECTRA
TRANSITION ELEMENT COMPLEXES
YIELDS
400201* - Chemical & Physicochemical Properties